反应 #1244306

反应方程式

ethyl (2S)-(3-chloro-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate

ammonia

→

ethyl (2R)-(3-amino-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate

收率 19.0%

溶剂

ethanol

反应条件

后处理

1. 1
   其他The solution was evaporated
2. 2
   其他the residue was purified by chromatography on a wet-packed silica gel column
3. 3
   洗涤eluting with methylene chloride/methanol (5-8% MeOH)
4. 4
   workup.ADDITIONcontaining 5% triethylamine
5. 5
   其他evaporated
6. 6
   workup.ADDITIONdiluted with methylene chloride and water
7. 7
   workup.ADDITIONThe aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3
8. 8
   萃取repeatedly extracted with methylene chloride
9. 9
   干燥The combined organic layers were dried over Na2SO4
10. 10
    其他evaporated

实验过程

A solution of ethyl (2S)-(3-chloro-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate (5.0 g, 17 mmol) in ethanol containing 9% of ammonia was stirred in an autoclave at room temperature for 6 days and at 55° C. for one further day. The solution was evaporated and the residue was purified by chromatography on a wet-packed silica gel column eluting with methylene chloride/methanol (5-8% MeOH) containing 5% triethylamine. The appropriate fractions were combined, evaporated and diluted with methylene chloride and water. The aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3 and repeatedly extracted with methylene chloride. The combined organic layers were dried over Na2SO4 and evaporated to give 0.9 g (19%) of ethyl (2R)-(3-amino-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate as a clear oil. Data: 1H NMR (500 MHz, CDCl3) δ 4.1-4.3 (m, 2H), 4.05 (b, 1H), 3.60-3.80 (m, 4H), 2.4-2.9 (m, 2H), 1.7-2.1 (m, 2H), 1.4-1.5 (dd,3H), 1.3-1.4 (m, 3H), 1.2 (m, 6H).

来源